


The First Time

by theinsandoutsofcastiel



Category: Supernatural
Genre: Anal Sex, F/M, NSFW, Oral Sex, Threesome, virgin!reader
Language: English
Status: Completed
Published: 2016-04-24
Updated: 2016-04-24
Packaged: 2018-06-04 05:49:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,633
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6643867
Author URL: https://archiveofourown.org/users/theinsandoutsofcastiel/pseuds/theinsandoutsofcastiel
Summary: <blockquote class="userstuff">
              <p>Hi there! You might be getting a lot of these lately, but can I request Sam x Dean x reader (no wincest) the reader is a virgin and accidentally spills the truth in being in love w/ both boys, and they are super sweet and gentle/slow with her? Thank you!</p>
            </blockquote>





	The First Time

Warnings: Language, virgin!Reader, smut, threesome, reader is slightly embarrassed by Dean’s dirty talk, oral, anal

Fic:

“I don’t think it’s a good idea for me to go on this hunt,” you say.

“Why not?” Sam asks, “You’ve never backed out on any hunts before.”

“You’re not afraid of dragons are you?” Dean asks before pausing, “Oh.”

“Don’t ‘oh’ me,” you complain.

“Y/N, are you a virgin?” Sam asks outright.

“What? No,” you scoff. Both boys give you a knowing look. “Yeah, I am ok?” you tell them, “I didn’t want to just lose it to anyone and neither of the men I love feel the same way about me.”

“What do you mean?” Dean asks.

“Nothing,” you respond, “Just go on the hunt and leave me behind.”

“How do you know these men don’t feel the same way?” Sam questions.

“They just don’t,” you answer, knowing you were only digging yourself a hole.

“Y/N, Sam and I love you,” Dean confesses.

“You - sorry, what?” you ask.

“You were talking about us right?” Sam asks.

“Did you just say you love me?” you ask, “Both of you?”

“Yeah,” Dean says shyly, looking away as he runs his hand through his hair, “We do.”

“You’re messing with me right?” you ask.

“Why would we mess with you?” Sam asks.

“I shouldn’t have said anything,” Dean adds.

“Why didn’t either of you ever tell me?” you question, “I wish I had known.”

“Why didn’t you tell us?” Sam asks.

“We’ve always loved you,” Dean explains, “But we didn’t think you felt the same way. We talked about it, a lot actually, and we decided that neither of us would make a move. We didn’t want to tell you that we loved you and make you feel like you had to choose between us.”

“And we didn’t want to drive you away either,” Sam adds, “We figured that if you loved one of us, you let us know; and if not, you’d let us know that too. We decided we’d accept it, no matter which of us you chose, if you even chose either of us.”

“I don’t think we ever really talked about the possibility of you liking both of us though,” Dean admits.

“This is …” you begin, but can’t seem to find the words.

“Crazy?” Dean offers.

“That’s one word for it,” you say.

“So, you know how we feel,” Sam says, “What about you?”

“I love both of you,” you admit. Both of them move closer.

“Would you be ok with us sharing you?” Dean asks. His hands reach out and run down your arms.

“You’d agree to share me?” you ask, honestly shocked by the proposition.

“We share a lot of things,” Sam says, his hands taking hold of your hips as he presses himself up against your back, “And I think I can speak for the both of us when I say I’d rather share you with my brother than not have you at all.”

“Dean?” you ask, wanting to hear his answer.

“Sam’s right,” Dean answers, “Maybe somewhere deep down neither of us wanted you to choose between us; maybe we wanted you to choose us both.”

“Then yes,” you tell them, “My answer is yes, I want both of you.”

“Are you sure?” Sam asks, “You don’t have to decide right away.”

“We’ll give you time to think about it if you want,” Dean agrees.

“I don’t need any more time,” you tell them, “I want you both and I’m ready for this.” To be honest, you’d thought about this a few times and you couldn’t deny that you wanted it.

Dean grins at you before taking your face between his hands and capturing your lips. Sam’s lips meet the skin of your neck, kissing you gently. You run your hands through Dean’s hair before reaching behind you to twist one hand into Sam’s. Dean’s tongue slides against your bottom lip and you easily grant him access. You moan as he deepens the kiss, his tongue exploring your mouth and mapping it out. His hands slide into your hair, encouraging you to tilt your head to the side, giving both him and Sam better access.

“I thought we agreed to share,” Sam mumbles against your skin. Sam’s hand comes up to cup your cheek, coaxing your lips away from Dean’s. As soon as he has your head turned towards him, Sam presses his lips to yours. Sam’s tongue explores your mouth just as Dean’s had, making you moan and whimper.

“We love you,” Dean mumbles against your skin. Two sets of lips and four hands travel over your body, making you melt between them. “Tell us you want this,” Dean mumbles, “We have to be sure.”

“I want this,” you assure him, mumbling against Sam’s lips, “I want both of you.”

“Good,” Sam whispers against your lips.

“Come here Baby Girl,” Dean says. His hands find yours and he coaxes you towards one of the motel beds and away from Sam. Sam grudgingly lets you slip between his fingers, but lets Dean pull you away. Dean sits you down on the edge of the bed, sitting beside you. “You okay Baby Girl?” Dean asks, “You look nervous.”

“I am, a little,” you admit, “It’s just, I’ve never been with one man, let alone two. I’m a little out of my element is all.”

“There’s no need to be nervous,” Sam says, sitting on your other side, “We’ll only go as far as you want us to. If you want us to stop all you have to do is tell us.”

“And we’ll be gentle,” Dean adds, “Since it’s your first time and all.” 

“Thanks for rubbing it in,” you say, slapping him on the shoulder.

“Just ignore him,” Sam says. He cups your cheek and guides your lips to his. His hand slides down your neck and along your shoulder. Dean moves closer, brushing your hair to the side before kissing the back of your neck. You sit still, letting them guide you since you’re not exactly sure what to do. Dean takes one of your hands and guides it to the base of the back of his neck. You slip your fingers into his hair. His hand slides down your arm as he leaves kisses against your skin.

Sam’s tongue swipes along your bottom lip, making you gasp. He takes the opportunity to slip his tongue between your lips, deepening the kiss. Sam guides your free hand to his chest, and you slide your hand up to his cheek. Their hands find their way to your body, moving slowly as they explore you. Dean’s fingertips dip beneath your shirt, his thumbs pressing circles against your skin. Your hands slide down to their shirts and fist in the material, begging them both to take off the layers. Sam pulls his hands from you and pushes his flannel shirt from his shoulders. He breaks the kiss in order to pull his t-shirt over his head.

Dean’s hands slide up further on your body, pressing flat against your skin. Heat seems to radiate from where he touches you. “Is this ok?” Dean asks, lifting the material slowly. You nod your head ‘yes,’ lifting your arms above your head and allowing Dean to pull the material from you. Dean casts the material to the side before pulling his own shirts from his body. Sam’s hands slide around to your back, his fingers playing with the clasp of your bra. His eyes search yours, asking for permission, which you willingly give. Your hands slide up his body as he pulls your bra from you.

Dean moves from the bed. The rustle of clothing hits your ears and you look over your shoulder to see Dean pushing down his pants and kicking off his shoes. Sam pulls your attention back to him as he takes hold of your hips and coaxes you to straddle his lap. “You’re so beautiful,” Sam whispers, his hands sliding up your sides and around to your back. He presses his hands flat against you and pulls you close as he captures your lips again. You feel Dean’s hands move to your hips and he tries to coax you away from Sam, but Sam isn’t so willing to let you go.

“What did we say about sharing Sammy?” Dean asks, “You want to be shared, don’t you Y/N?”

“Yes,” you mumble against Sam’s lips. Sam groans against your lips and reluctantly lets Dean pull you from him. Dean helps you from the bed and pulls you against him, his naked body pressed right up against you. Sam places one hand on the bed behind him and leans back as he palms the bulge in his pants. Dean rocks his hips forward, his hard cock pressing against your jean clad ass.

Reaching behind you with both hands, you twist your fingers into Dean’s hair. His lips press soft kisses against the skin of neck and shoulder. You moan as Dean’s hands slide down your body, stopping to grope your breasts. Sam watches your reaction, gnawing on his bottom lip as you squirm beneath Dean’s hands. One of his hands slowly moves lower and lower on your body until his fingertips meet the waistband of your pants.

With one hand, Dean deftly unbuttons your pants and pulls down the zipper. His hands slip beneath the waistband of your pants and he helps you shimmy out of them as you kick off your shoes and toe off your socks. Sam’s eyes become darker as he watches the way you move, his hand pressing harder against the bulge in his pants. “Come here Baby Girl,” Dean whispers in your ear. You let him guide you back towards the bed and he sits down, his back resting against the headboard. Sam stands from the bed, his hands working at the button of his pants. Dean holds out a hand to you and he guides you onto the bed so that you’re settled between his legs, resting with your back against his front. “You’re so sexy,” Dean whispers in your ear, his hands traveling over your body. His lips kiss and his teeth nip at your skin.

You watch wide eyed as Sam pushes his pants and boxers down, his hard cock springing free. Dean’s hands knead your breasts, his fingers pinching and rolling your nipples. “You doing ok Baby Girl?” Dean asks.

“Yes,” you answer breathlessly, watching as Sam crawls onto the bed. One of Sam’s hands slides up your leg while his lips leave a trail of kisses up the other.

“Tell us what you want,” Dean prompts, nestling his face into the crook of your neck.

“You, both of you,” you tell them, squirming beneath their touches. One of Dean’s hands travels down your body and his fingers slip beneath the waistband of your panties. His fingers brush your clit, making your hips buck towards his hand.

“Like this?” Dean asks, “Is this how you want us?” Sam smirks against your skin as he kisses higher and higher on your thigh.

“Dean,” you complain, wiggling against him. Dean groans as you press back against his hard cock. He presses his fingers harder against your clit, making you moan and whimper. “Please,” you whisper, clutching at both Sam and Dean.

“Please what?” Dean asks, “You want our cocks inside you don’t you? Want us to fuck you?” You can feel a blush rising to your cheeks.

“It’s ok,” Sam says, his eyes flicking up to see your blush, “You don’t have to be embarrassed.”

“I’m not,” you protest, swallowing hard as Dean runs his fingers along your wet folds.

“You’re so wet for us,” Dean whispers in your ear, making your blush deepen, “I bet you taste so sweet.” A moan escapes your lips as Dean pushes his middle finger inside you, swirling it against your walls. Sam begins kissing down your other thigh, making your skin heat up with each kiss he leaves.

“You like that?” Sam asks, his eyes flicking up to watch your expression.

“Yes,” you moan, “It feels good, so good.” You rock your hips into Dean’s hand, loving the way he touched you. Sam shifts on the bed, settling down before pulling your panties to the side. His eyes lock onto yours as he presses his middle finger into you, curling it. The two of them fall into a rhythm that has one of them inside you at all times. They curl their fingers against your g-spot, making you desperate and needy.

You groan in disapproval as Dean pulls his finger from you. He brings it up to his lips and you watch as he sucks the digit clean. “Just like I thought,” Dean tells you, “You taste so sweet. You really should taste her Sam.”

Much to your disappointment, Sam pulls his finger from you as well. He hums as he sucks the digit clean. “Damn,” Sam hums, “You do taste good.” Sam hooks his fingers beneath the waistband of your panties, pulling them down. You lift your hips to help him. As soon as the material is gone, Sam settles back down between your legs and leaves a long lick along your pussy lips.

“Sam!” you moan as he sucks your clit between his lips. Sam pushes two fingers into you again, scissoring them and curling them against your g-spot. Dean cups your breasts in his hands, kneading them as Sam licks and sucks at your slick folds.

“Get her ready for me Sammy,” Dean mumbles against your skin. He rocks his hips against you, his hard cock leaking precum onto his abdomen and making your skin stick to his. Sam pulls his fingers from you, rubbing them around the tight ring of muscles of your asshole. His fingers are slick with your juices, making it easier to for him to slide his fingers into your tight hole.

“Sam,” you groan at the strange feeling of him stretching you out. His tongue delves into your pussy as he buries his face between your legs. “Oh Sam,” you moan, rocking your hips against him. Your hands move to his hair, fisting into the locks.

“That’s it,” Dean encourages you, “Ride Sammy’s tongue. Show him just what you want.” Dean rocks his hips against you, pushing you closer to Sam each time. “You’re gonna feel so full,” Dean whispers in your ear, “It’s gonna feel so good with both of us inside you.” Sam rocks his hips against the bed, searching for friction for himself. Sam slides a third finger into your ass, stretching you wider. “Good girl,” Dean praises, “You’re gonna take us so well.” Sam licks up your pussy lips again and sucks your clit into his mouth, drawing the bundle of nerves out between his teeth. The feelings of their hands on you and inside you combined with Dean’s words make your stomach twist.

“Cum for me,” Sam mumbles against you, sending vibrations straight to your core. His fingers pump in and out of you slowly, pressure building in your stomach as he swirls his tongue against your pussy walls again. The two of them build you higher and higher, your walls growing tight as the knot in your stomach pulls tight.

“Go ahead,” Dean prompts, “Cum for us, cum around Sammy’s tongue.”

“Sam, Dean,” you moan. Dean kisses the sweet spot behind your ear at the same time Sam nudges his nose against your clit, sending you over the edge. “Oh Sam!” you cry out, “Dean!” Dean turns your face towards his, capturing your lips and swallowing the sounds you make. Your walls clamp down around Sam’s tongue and fingers. Dean holds you to him as your body shudders from the intensity of your orgasm.

“How was that?” Sam asks, his lips kissing the skin of your thighs as he pulls his fingers from you.

“Good,” is the only response you can think, “So good.”

“Only good?” Dean asks, “We’re going to have to do something about that.” Sam leans over to the chair beside the bed and grabs his hunting bag, pulling out a box of condoms and a bottle of lube. He sits up on his knees between your legs and pulls out two condoms before tossing the box to the side. Sam tosses the second condom and the bottle of lube to Dean before tearing open the package of his own condom and rolling it over his cock, the tip glistening with precum.

“Here,” Sam says, extending his hand to you. He helps you up to your knees and pulls you to him, occupying you as Dean gets himself ready. “Are you sure you’re ready for this?” Sam asks, making sure you’re comfortable.

“Yes,” you tell him, “I want this.” You lean in and kiss Sam, your hands exploring his body. “I want both of you,” you mumble against his lips. Sam’s hands find your hips and he pulls you closer, his hard cock sliding through you dripping folds.

“Tell me if you need me to stop,” Sam tells you, and you nod, telling him you understand. Sam wraps one hand around his cock and lines it up with your entrance. He captures your lips and distracts you as he pushes into you slowly and fills you inch by throbbing inch. The feeling is strange and a little uncomfortable at first, but it quickly turns to pleasure as you adjust to his size.

Dean slots himself in behind you, his fingers slick with lube pressing against your asshole. “I’ll go slow,” Dean promises. You feel him press his swollen tip against your back entrance and push into you. Your walls stretch as he pushes just his tip inside you. He lets you adjust before pushing a little farther into you, his hands grasping your ass cheeks and spreading you to give him better access. Sam struggles to stay still as his brother fills you to the hilt, making you feel full and tight around both of them. Dean kisses the back of your neck and shoulders as Sam kisses your lips, both of them occupying and distracting you as you adjust to having them both inside you.

“Let us know when you’re ready,” Sam mumbles against your lips. Dean’s hands slide around to the front of your body, cupping your breasts again and kneading the flesh. He pulls you back against him, the hard lines of his body pressed up against you. When you’re ready, you wiggle your hips experimentally, lifting them before sinking back down onto the two cocks inside you.

“Oh fuck,” you whisper as their cocks fill you once again, “You feel so good.”

“She means me by the way,” Dean says with a smirk.

“In your dreams,” Sam responds. You can’t help but laugh at the competition between them.

The boys each set a slow pace, one complementing the other. As Sam slides out of you, Dean slides in and vice versa, one of them always buried deep inside you. Sam’s head ducks down, sucking one of your nipples between his lips.

“You’re doing so well,” Dean praises, his fingertips pressing into your skin. You practically melt between them, loving the way they felt inside you, the way their hands felt on your skin, the way their lips moved against you. They silently fight for your attention, trying to earn your kisses and moans.

“Dean, Sam,” you moan, your walls growing tight around their throbbing cocks. Your hands fist in their hair, tugging lightly. “Please,” you moan, “I’m close.”

“We know,” Sam mumbles against you.

“We can feel how tight you are,” Dean says. Their cocks twitch inside you, making you moan.

Their paces alter and fall out of rhythm, both of them filling you at the same time. You could tell they were holding back, doing their best to be as gentle with you as they could be. They work you higher and higher, bringing you closer and closer to the precipice. Their names fall from your lips like a prayer.

“That’s it,” Sam praises as your walls begin to flutter around them, “You feel so good.” One of Dean’s hands slides down your body and finds your clit, rubbing slow, deliberate circles around the bundle of nerves. The knot in your stomach pulls tight and snaps again.

“Oh, Sam! Dean!” you cry out as your orgasm washes over you. Your walls clamp down around their throbbing cocks, drawing them into the depths with you.

“Y/N, fuck,” Dean groans as his cock pulses, Sam following right after with a shout of “Y/N!” They both push all the way into you, filling you completely as their cocks pulse and spill themselves into the condoms. Their orgasms prolong yours, your walls squeezing their cocks and milking them for all they’re worth. They hold you as your body slumps, their muscles tensing and relaxing around you.

They kiss you as they work you through your high, both of them caressing each inch of your body that they can reach. “How was that?” Dean asks, his lips brushing the shell of your ear.

“Amazing,” you answer.

“Amazing? That’s it?” Sam chides.

“Surely we can do better than that, can’t we Sammy?” Dean asks. They pull themselves from you gently and lie you back against the bed, both of them looming over you.

“I guess we’ll just have to try harder won’t we?” Sam asks, exchanging a sly look with Dean before they both look down on you with dark eyes. Their looks have you gnawing on your bottom lip.

“Do you want that Y/N?” Dean ask.

“Fuck, yes,” you answer. Both of them smirk before leaning down over you, devoting all their attention to you.


End file.
